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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2013-07-04 18:59:24 UTC
Update Date2019-07-23 07:15:05 UTC
HMDB IDHMDB0060787
Secondary Accession Numbers
  • HMDB60787
Metabolite Identification
Common Name6-Methoxy-2-naphthylacetic acid
Description6-Methoxy-2-naphthylacetic acid belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups. Nabumetone is a non-steroidal anti-inflammatory drug (NSAID), the only 1-naphthaleneacetic acid derivative. 6-Methoxy-2-naphthylacetic acid is a very strong basic compound (based on its pKa). 6-Methoxy-2-naphthylacetic acid is a metabolite of nabumetone. Nabumetone has been developed by Beecham. It is available under numerous brand names, such as Relafen, Relifex and Gambaran.
Structure
Data?1563866105
Synonyms
ValueSource
6-Methoxy-2-naphthylacetateGenerator
Chemical FormulaC39H37NO12
Average Molecular Weight711.7106
Monoisotopic Molecular Weight711.231575653
IUPAC Name2-[(2S,4S)-4-[(4-amino-5-hydroxy-6-methyloxan-2-yl)oxy]-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-1,2,3,4,6,11-hexahydrotetracen-2-yl]-2-oxoethyl 2-(naphthalen-1-yl)acetate
Traditional Name2-[(2S,4S)-4-[(4-amino-5-hydroxy-6-methyloxan-2-yl)oxy]-2,5,12-trihydroxy-7-methoxy-6,11-dioxo-3,4-dihydro-1H-tetracen-2-yl]-2-oxoethyl 2-(naphthalen-1-yl)acetate
CAS Registry NumberNot Available
SMILES
COC1=CC=CC2=C1C(=O)C1=C(C(O)=C3C[C@](O)(C[C@H](OC4CC(N)C(O)C(C)O4)C3=C1O)C(=O)COC(=O)CC1=CC=CC3=CC=CC=C13)C2=O
InChI Identifier
InChI=1S/C39H37NO12/c1-18-34(43)24(40)14-29(51-18)52-26-16-39(48,27(41)17-50-28(42)13-20-9-5-8-19-7-3-4-10-21(19)20)15-23-31(26)38(47)33-32(36(23)45)35(44)22-11-6-12-25(49-2)30(22)37(33)46/h3-12,18,24,26,29,34,43,45,47-48H,13-17,40H2,1-2H3/t18?,24?,26-,29?,34?,39-/m0/s1
InChI KeyGYCQOHQXGJAWAC-XFZKEZEPSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as hydroxybenzoic acid derivatives. Hydroxybenzoic acid derivatives are compounds containing a hydroxybenzoic acid (or a derivative), which is a benzene ring bearing a carboxyl and a hydroxyl groups.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentHydroxybenzoic acid derivatives
Alternative Parents
Substituents
  • Dihydroxybenzoic acid
  • Isobenzofuranone
  • Phthalide
  • Isocoumaran
  • Medium-chain fatty acid
  • Branched fatty acid
  • Heterocyclic fatty acid
  • Hydroxy fatty acid
  • Methyl-branched fatty acid
  • Dicarboxylic acid or derivatives
  • Fatty acyl
  • Unsaturated fatty acid
  • Fatty acid
  • Vinylogous acid
  • Lactone
  • Carboxylic acid ester
  • Oxacycle
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Organic oxygen compound
  • Organooxygen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Carbonyl group
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External DescriptorsNot Available
Ontology
Disposition

Source:

Biological location:

Role

Biological role:

Physical Properties
StateNot Available
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
LogPNot AvailableNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.018 g/LALOGPS
logP2.95ALOGPS
logP4.18ChemAxon
logS-4.6ALOGPS
pKa (Strongest Acidic)9.53ChemAxon
pKa (Strongest Basic)8.94ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count12ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area212.14 ŲChemAxon
Rotatable Bond Count9ChemAxon
Refractivity184.92 m³·mol⁻¹ChemAxon
Polarizability73.9 ųChemAxon
Number of Rings7ChemAxon
BioavailabilityNoChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-4900200000-9d7949be4a71ca079fb4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-02u3-0602194300-a1d03a1222aa72394718Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-015a-0904171000-43793ae7cbc3a354be20Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-00mo-3906011000-f70870016b3535f63bc6Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-029i-0900031200-30f6ee120a88e645fe01Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-00kr-0901010000-1590cf5fe3d4bac188dbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-00kr-0901000000-de625c9bcbff1ac9e825Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane (predicted from logP)
Biospecimen Locations
  • Blood
  • Urine
Tissue Locations
  • Kidney
  • Liver
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableNormal
    details
    UrineExpected but not Quantified Not AvailableNot AvailableNormal
      details
      Abnormal Concentrations
      Not Available
      Associated Disorders and Diseases
      Disease ReferencesNone
      Associated OMIM IDsNone
      DrugBank IDNot Available
      Phenol Explorer Compound IDNot Available
      FooDB IDNot Available
      KNApSAcK IDNot Available
      Chemspider IDNot Available
      KEGG Compound IDNot Available
      BioCyc IDNot Available
      BiGG IDNot Available
      Wikipedia LinkNot Available
      METLIN IDNot Available
      PubChem Compound24195890
      PDB IDNot Available
      ChEBI IDNot Available
      Food Biomarker OntologyNot Available
      VMH IDNot Available
      References
      Synthesis ReferenceNot Available
      Material Safety Data Sheet (MSDS)Not Available
      General ReferencesNot Available